Tag: M.W=200-300

Related Products of 118289-55-7, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 118289-55-7, name is 6-Chloro-5-(2-chloroethyl)indolin-2-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A mixture of 6-chloro-5-(2-chloroethyl)-1,3-dihydro-2H-indol-2-one 1 (1.00mol), potassium carbonate (1.20mol), secondary amine (2a-h, 1.30mol) in water (10mL) was refluxed until completion (TLC, about 24-48h) and the reaction mass was cooled to RT and then extracted with DCM to get crude 3a-h. Recrystallized using aqueous acetone or aqueous ethanol or methanol (Yield 55-70%).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 6-Chloro-5-(2-chloroethyl)indolin-2-one, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Meti, Gangadhar Y.; Kamble, Atulkumar A.; Kamble, Ravindra R.; Somagond, Shilpa M.; Devarajegowda; Kumari, Sandhya; Kalthur, Guruprasad; Adiga, Satish K.; European Journal of Medicinal Chemistry; vol. 121; (2016); p. 221 – 231;,
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Reference of 6780-38-7,Some common heterocyclic compound, 6780-38-7, name is 2-(1,3-Dioxoisoindolin-2-yl)acetyl chloride, molecular formula is C10H6ClNO3, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

To a solution of Boc-hydrazine (7.08. g, 53.5 mmol) in DCM (200 mL) was added Et3N (13.5 mL, 97.4 mmol) , and then compound 651 (10.8 g, 48.7 mmol) was added at 0 . After that the reaction was stirred at r.t. for 30 min. and poured into ice-water (100 mL) and extracted with DCM (3 ¡Á 100 mL) . The combined organic phases were washed with water (100 mL) and brine (100 mL) , dried over anhydrous Na2SO4, filtered and concentrated to give a white solid (15.5 g, 100%yield) . ESI m/z calcd for C15H18N3O5[M+H]+: 320.12, found: 320.12.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(1,3-Dioxoisoindolin-2-yl)acetyl chloride, its application will become more common.

Reference:
Patent; HANGZHOU DAC BIOTECH CO. LTD; ZHAO, Robert Yongxin; YANG, Qingliang; HUANG, Yuanyuan; ZHAO, Linyao; GAI, Shun; YE, Hangbo; LEI, Jun; XU, Yifang; CAO, Mingjun; GUO, Huihui; JIA, Junxiang; TONG, Qianqian; LI, Wenjun; ZHOU, Xiaomai; XIE, Hongsheng; BAI, Lu; CAI, Xiang; ZHUO, Xiaotao; ZHANG, Xiuzheng; ZHENG, Jun; (424 pag.)WO2019/127607; (2019); A1;,
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954-81-4, name is N-(5-Bromopentyl)phthalimide, belongs to indolines-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Product Details of 954-81-4

General procedure: 2-(omega-Bromoalkyl)-isoindoline-1,3-dione (1 equiv) with N-methylbenzylamine (1 equiv) or its substituted analog in the presence of K2CO3 (3 equiv) was stirred in acetonitrile under reflux for 16 h. Once the reaction was finished, the solvent was evaporated under vacuum, producing a residue that was further dissolved in 50 mL of 5 M NaOH and extracted with ethyl acetate (3 x 50 mL). The combined organic extracts were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (dichloromethane to dichloromethane/methanol 98:2), yielding a yellow oil. The final product was obtained in the form of hydrochloride salt. The following compounds were obtained.

The synthetic route of 954-81-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Guzior, Natalia; Bajda, Marek; Rakoczy, Jurand; Brus, Boris; Gobec, Stanislav; Malawska, Barbara; Bioorganic and Medicinal Chemistry; vol. 23; 7; (2015); p. 1629 – 1637;,
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In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 5332-26-3 as follows. Recommanded Product: 5332-26-3

General procedure: The vacuum dried intermediate 3 (0.002 mol) was then reacted with mono- and di-substituted benzoic acids (0.003 mol) separately in presence of anhydrous potassium carbonate (0.003 mol) in DMF (10 mL). The reaction mixture was stirred at room temperature for about 2 h. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was poured into ice-cold water and allowed stir for 10 min. The solid obtained was filtered and washed successively with distilled water and recrystallized from ethanol to obtain4(a-n).

According to the analysis of related databases, 5332-26-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Kumar, C.S. Chidan; Loh, Wan-Sin; Chandraju, Siddegowda; Win, Yip-Foo; Tan, Weng Kang; Quah, Ching Kheng; Fun, Hoong-Kun; PLoS ONE; vol. 10; 3; (2015);,
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Reference of 5332-26-3, A common heterocyclic compound, 5332-26-3, name is 2-(Bromomethyl)isoindoline-1,3-dione, molecular formula is C9H6BrNO2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

(3a) To a THF (20 mL) solution of dimethyl methylmalonate (5.5 g, 37 mmol) at -10 C. was added NaH (60% in mineral oil, 1.66 g, 1.1 eq). The mixture was stirred for 20 min, then N-bromomethylphthalimide (9.5 g, 1.05 eq) was added at 0 C. The mixture was allowed to slowly warm to rt, stirred for 3 h, and quenched with water. Following extraction with ethyl acetate, the combined ethyl acetate extracts were washed with 1 N HCl and brine, dried (MgSO4), filtered and concentrated. Purification by flash column chromatography (20% ethyl acetate-hexane) yielded the phthalimide as a white crystalline solid (5.81 g, 51%).

The synthetic route of 5332-26-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Duan, Jingwu; Jiang, Bin; Chen, Lihua; Lu, Zhonghui; Barbosa, Joseph; Pitts, William J.; US2003/229084; (2003); A1;,
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In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 20870-78-4 as follows. Application In Synthesis of 5-Bromoindolin-2-one

A mixture of 28b (513mg, 2.42mmol), 4,4,5,5-tetramethyl-2-(4,4,5,5- tetramethyl (l,3,2-dioxaborolan-2-yl))-l ,3,2-dioxaborolane (716mg, 2.82mmol) and KOAc (878mg, 8.95mmol) in dioxane (2OmL) was purged with nitrogen for lOmin, then added Pd(dppf)Cl2. CH2Cl2 (108mg, 0.13mmol). The resulting mixture was stirred at 800C overnight and evaporated. The residue was dissolved in ethyl acetate and filtrated. The filtrate was washed with brine (15mLchi2), dried over Na2SO4 and concentrated. The residue was purified by column chromatography (EA: PE =4:1) to afford 28c (470mg, 75%).

According to the analysis of related databases, 20870-78-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; XCOVERY, INC.; WO2008/88881; (2008); A1;,
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These common heterocyclic compound, 132898-96-5, name is 2,3-Dioxoindoline-5-sulfonyl chloride, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. category: indolines-derivatives

The hydrochloride salt of racemic 3-fluoropyrrolidinc (628 mg, 5mmol) was added to a solution of 2,3-oxoindohne-5-sulfonyl chloride (1.2 g, 4.9 mmol) and diisopropylethyl amine (2.6 mL, 15 mmol) in 1 :1 CH2Cl2ZTHF (50 mL) at -50 C. The solution was warmed to room temperature and slirred at that temperature for 12 hours. The reaction mixture was concentrated, dissolved in CII2CI2. and then washed with saturated NaHCO3 and brine. I he organic layer was dried (MgSO4), filtered, concentrated, and purified by flash chromatography on silica gel (5% MeOH in CH2Cl2) to provide 1.4 g of the product as an orange solid

The synthetic route of 2,3-Dioxoindoline-5-sulfonyl chloride has been constantly updated, and we look forward to future research findings.

Reference:
Patent; WYETH LLC (FORMERLY KNOWN AS WYETH); DOLLINGS, Paul, Jeffrey; DONNELL, Andrew, Forrest; GILBERT, Adam, Matthew; ZHANG, Minsheng; HARRISON, Boyd, Lynn; STANTON III, Charles, John; O’NEIL, Steven, Victor; HAVRAN, Lisa, Marie; CHONG, Dan, Chaekoo; WO2010/77839; (2010); A1;,
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Reference of 5332-26-3, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 5332-26-3, name is 2-(Bromomethyl)isoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows.

A suspension of N-(bromomethyl)phthalimide (3.6g, 15.0mmol) in triethylphosphite (3.00g, 18.0mmol) was heated to 90Cfor 3h. A distillation apparatus was then installed and volatile ethyl bromide was removed by reduced pressure distillation. The crude mixture was cooled to room temperature, and the resulting white solid was used without further purification. 1H NMR (300MHz, CDCl3) delta=1.24 (t, J=7.1Hz, 6H, 2¡ÁCH3), 4.01 (d, 2JH-P=11.4Hz, 2H, 1¡ÁCH2), 4.12 (m, 4H, 2¡ÁCH2), 7.73 (dd, J=5.5, 3.1Hz, 2H, 2¡ÁCH), 7.86 (dd, J=5.3, 3.0Hz, 2H, 2¡ÁCH) ppm. To a solution of this solid (4.5g, 15mmol) in ethanol (20mL) was added hydrazine monohydrate (1.05mL, 21.6mmol) and the resulting mixture was stirred at room temperature overnight, and then refluxed for 3h. The crude mixture was cooled down to 0C, and the white precipitate was removed by filtration and washed with ice-cold ethanol. The solution was concentrated under vacuum, and the resulting oily residue was purified by column chromatography on silica gel eluting with a gradient of Et2O/ MeOH (80:20?70:30) to afford compound 24 as a pale yellow oil (2.43g, 97%). TLC: Rf=0.30 (silica gel, Et2O/MeOH 80:20, stained with ninhydrin). 1H NMR (300MHz, CD3CN) delta=1.31 (t, J=7.1Hz, 6H, 2¡ÁCH3), 1.76 (br, 2H, NH2), 2.94 (d, 2JH-P=10.6Hz, 2H, 1¡ÁCH2), 4.08 (quintet, 3JH-H=3JH-P=7.0Hz, 2H, 1¡ÁCH2), 4.10 (quintet, 3JH-H=3JH-P=7.1Hz, 2H, 1¡ÁCH2) ppm. 31P NMR (121MHz, CDCl3) delta=27.49ppm.

The chemical industry reduces the impact on the environment during synthesis 2-(Bromomethyl)isoindoline-1,3-dione. I believe this compound will play a more active role in future production and life.

Reference:
Article; Leygue, Nadine; Perez e Iniguez De Heredia, Aritz; Galaup, Chantal; Benoist, Eric; Lamarque, Laurent; Picard, Claude; Tetrahedron; vol. 74; 31; (2018); p. 4272 – 4287;,
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Related Products of 3416-57-7, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 3416-57-7, name is 2-(2-Oxopropyl)isoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a solution of l-[4-(trifluoromethyl)phenyl]methanamine (1.7 g, 9.7 mmol, 1.5 equiv) in trifluoroethanol (10.0 mL) was added 2-(2-oxopropyl)isoindoline-l,3-dione (2.0 g, 9.6 mmol, 1.5 equiv). After stirring at r.t. for 10 min, to the mixture was added 5-chloro-3- fluoro-2-isocyanopyridine (1.0 g, 6.4 mmol, 1.0 equiv) and chloroacetic acid (899.4 mg, 9.5 mmol, 1.5 equiv). The resulting mixture was stirred at 60 C overnight, concentrated under vacuum, and purified by C18 column, eluted with water (0.5%NH4HCO3)/ACN (1/5) to afford 750 mg of /V-(5-chloro-3-fluoropyridin-2-yl)-2-(2-chloro-/V-[[4- (trifluoromethyl)phenyl]methyl]acetamido)-3-(l,3-dioxoisoindol-2-yl)-2-methylpropan amide (Intermediate 64-2) as a yellow oil. LRMS (ES) m/z 611 (M+H).

The synthetic route of 2-(2-Oxopropyl)isoindoline-1,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CYTOKINETICS, INC.; CHUANG, Chihyuan; MORGAN, Bradley P.; VANDERWAL, Mark; ASHCRAFT, Luke W.; LAU, Kevin; (455 pag.)WO2020/47447; (2020); A1;,
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5394-18-3, name is 2-(4-Bromobutyl)isoindoline-1,3-dione, belongs to indolines-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. COA of Formula: C12H12BrNO2

General procedure: To a mixture of the corresponding R1R2NH (3.0 mmol), anhydrous K2CO3 (449 mg, 3.25 mmol) and KI (20.75 mg, 0.125 mmol) in CH3CN (12 ml) were added the appropriate intermediates 6-9 (2.5mmol). The reaction mixture was warmed to 60-65 C and stirred for 6-8 h under an argon atmosphere. After complete reaction, the solvent was evaporated under reduced pressure. Then water (25 mL) was added to the residue and the mixture was extracted with dichloromethane (25 mL¡Á3). The combined organic phases were washed with saturated aqueous sodium chloride (30 mL), dried over sodium sulfate, and filtered. The solvent was evaporated to dryness under reduced pressure. The residue was purified on a silica gel chromatography using mixtures of petroleum ether/EtOAc as eluent, obtaining the corresponding intermediates 10-13a-d.

The synthetic route of 5394-18-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Li, Yuxing; Qiang, Xiaoming; Li, Yan; Yang, Xia; Luo, Li; Xiao, Ganyuan; Cao, Zhongcheng; Tan, Zhenghuai; Deng, Yong; Bioorganic and Medicinal Chemistry Letters; vol. 26; 8; (2016); p. 2035 – 2039;,
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